Carbohydrate chemistry dipolar cycloadditions

Santoyo-Gonzdlez F, Hernandez-Mateo F (2007) Azide-Alkyne 1,3-Dipolar Cycloadditions a Valuable Tool in Carbohydrate Chemistry. 7 133-177 Saraboji K, see Ponnuswamy MN (2006) 3 81-147... 

Click chemistry has been particularly active in various fields this year. For example, ample applications of click chemistry have been seen in carbohydrate chemistry. Various /weiido-oligosacchardies and amino acid glycoconjugates were synthesized via an intermolecular 1,3-dipolar cycloaddition reaction using easily accessible carbohydrate and amino acid derived azides and alkynes as building blocks <06JOC364>. The iterative copper(I)-catalyzed... 

F. Santoyo-Gonzalez and F. Hemandez-Mateo, Azide-alkyne 1, 3-dipolar cycloadditions A valuable tool in carbohydrate chemistry, Top. Heterocycl. Chem., 7 (2007) 133-177. 

S. Dedola, S. A. Nepogodiev, and R. A. Field, Recent applications of the Cul-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry, Org. Biomol. Chem.., 5 (2007) 1006-1017. 

Celine Cano-Soumillac was born in Angouleme, France, in 1977. She studied Organic Chemistry at the University of Poitiers, France. In 1999, she went to Paris as a predoctoral fellow and worked on asymmetric synthesis of substituted piperazines from phenylglycinol derivatives, under the supervision of Prof. H.-P. Husson. In 2000, she moved back to Poitiers, where she worked on the synthesis of biomolecules by 1,3-dipolar cycloadditions with carbohydrates and received her Ph.D. degree in 2004. She then joined the group of Prof John A. Joule at the University of Manchester, UK as a postdoctoral fellow and worked on the synthesis of analogues of cofactors of oxomolybdoenzymes. She now holds a research associate position in the Northern Institute for Cancer Research, at Newcastle University, UK, where she works on the synthesis of inhibitors of DNA-dependent protein kinase. Her research interests include heterocyclic chemistry, carbohydrates chemistry, asymmetric synthesis, and development of new synthetic methodologies. 

Click chemistry has also been applied in carbohydrate chemistry. Thus, Huisgen cyclization involving a sugar azide or alkyne has been extensively used for the preparation of a wide range of carbohydrates bearing a triazole moiety in different positions. In this volume, Santoyo Gonzalez and Herndndez-Mateo present a contribution concerning azide-alkyne 1,3-dipolar cycloadditions, mostly devoted to non-anomeric positions. 

Azide-Alkyne 1,3-Dipolar Cycloadditions a Valuable Tool in Carbohydrate Chemistry... 

A review of cycloaddition reactions in carbohydrate chemistry is presented. The use of carbohydrate-derived dienes and dienophiles in the Diels-Alder reaction, hetero-Diels-Alder and dipolar addition reactions of carbohydrates are described. Stereochemical aspects of the cycloaddition processes are also discussed, and applications to the synthesis of natural products are included for each reaction type. Much of the material presented has appeared in the literature within the past five years however, earlier studies are also included in order to give a more representative historical perspective. 

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